Caleb Nakamura

Associate, Corporate

Start-up lawyer who speaks fluent term sheet and plain English.

“If I can't explain a clause in one sentence, it probably shouldn't be in your contract.”

Email: [email protected]
Direct line: +1 (312) 555-0218
Office: Chicago
With the firm since: 2022

Caleb's story

Caleb grew up in Sacramento, the son of a Japanese-American father who ran an almond orchard and a mother who taught middle-school maths. He spent summers driving a forklift in the packing shed and learned to negotiate from watching his father deal with the co-op.

He studied economics at UC Davis, spent three years at a start-up accelerator in San Francisco helping founders prepare for investment, and realised that the lawyers in the room were the ones who actually understood what was being agreed. He went to law school at the University of Chicago and joined Hale & Mercer straight after graduating in 2022.

His first solo matter was a 2024 seed round for a two-founder logistics software company in the West Loop. The investors' first draft would have given them control at the next round; Caleb rewrote the protective provisions, explained every clause to the founders in a single page, and the deal closed in three weeks. The company has since raised twice more.

Caleb lives in Wicker Park with his partner Jess, a nurse anaesthetist, and plays in a Tuesday-night basketball league at the Wicker Park fieldhouse. He is the firm's unofficial technology help desk and does not mind.

Off duty

When Caleb isn't at the office

Backcountry backpacking

Has hiked 400 miles of the Pacific Crest Trail in sections and plans to finish before he is forty. He packs lighter every year and still carries a paperback.

Film photography

Shoots on a 1978 Pentax K1000 that belonged to his father and develops black-and-white film in a converted bathroom. The firm's holiday card has been his for two years running.